Diphenyl chlorophosphate (HCID 75654)

Überblick

Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.

Namen und Bezeichner

Bevorzugter Name: Diphenyl chlorophosphate
IUPAC: [chloro(phenoxy)phosphoryl]oxybenzene
Lokaler Name: Diphenylchlorphosphat
Englischer Name: Diphenyl chlorophosphate
Summenformel: C12H10ClO3P
Molmasse: 268.63

Namen und Synonyme

Diphenyl chlorophosphate2524-64-3Diphenyl phosphorochloridatediphenyl chlorophosphonateDiphenylphosphoryl chlorideChlorodiphenoxyphosphine oxidePhosphorochloridic acid, diphenyl esterDiphenoxychlorophosphine oxideO,O-Diphenyl chlorophosphateDiphenylphosphoric acid monochlorideDiphenyl phosphochloridatePhosphoric acid chloride diphenyl ester

Weitere Namen anzeigen

DPCPCHLOROPHOSPHORIC ACID DIPHENYL ESTERDPOCDiphenylchlorophosphonateDiphenyl chloridophosphateDCP:DPCP(PhO)2POCIAURORA KA-1636

DiphenylphosphorylchloridateDTXSID2044892Phenyl phosphorochloridate ((PhO)2ClPO)1KEE9757OTNSC-43771DIPHENYL PHOSPHOROCHLORATEDTXCID0024892PHENYL PHOSPHOROCHLORIDITE

Datenbank-Bezeichner

CAS: 2524-64-3
PubChem CID: 75654
DTXSID: DTXSID2044892
ChEMBL: CHEMBL3188224
UNII: 1KEE9757OT
EC Number: 219-759-6
Nikkaji: J7.599J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,5
Polarare Oberfläche (TPSA): 35,5 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 4
Schwere Atome: 17
Formalladung: 0
Komplexität: 249

Experimentelle und physikochemische Eigenschaften

Density1.296 @25 °C

Physical Description · 2 Einträge

Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.

Liquid

Physikochemische Eigenschaften

Siedepunkt: 314 · 314-316 °C/272 mmHg (lit.)
Dichte: 1.296 g/mL · 1.296 g/mL at 25 °C (lit.)
Dampfdruck: 10 mm · 10 mm Hg ( 190 °C)
Brechungsindex: 20 · n20/D 1.55(lit.)
Flammpunkt: 230 °F · >230 °F
storage temp.: 2 · Inert atmosphere,2-8°C
Löslichkeit: Chloroform (Slightly), DMSO (Slightly)
Aggregatzustand: Liquid
Farbe: Clear colorless to light yellow
Wasserlöslichkeit: MAY DECOMPOSE
BRN: 654130 · 654130
Henry's Law Constant: 3.7 · 3.7×10-2 mol/(m3Pa) at 25℃, Bartelt-Hunt et al. (2008)
Stabilität: Stable under recommended storage conditions., Stable Under Recommended Storage C
InChI: 1S/C12H10ClO3P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
InChIKey: BHIIGRBMZRSDRI-UHFFFAOYSA-N
SMILES: ClP(=O)(Oc1ccccc1)Oc2ccccc2
CAS Datenbank: 2524 · 2524-64-3(CAS DataBase Reference)
NIST chemische Informationen: Diphenyl chlorophosphate(2524-64-3)
EPA chemische Informationen: Phosphorochloridic acid, diphenyl ester (2524-64-3)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (69.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 166 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Phosphorochloridic acid, diphenyl ester

Phosphorochloridic acid, diphenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorochloridic acid, diphenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19780

Diphenyl phosphorochloridate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive

Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Reactivity Profile · 1 Eintrag

DIPHENYL CHLOROPHOSPHATE is incompatible with bases (including amines) strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. May form highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Protective Action Criteria (PAC) · 3 Einträge

7.9 [mg/m3]

87 [mg/m3]

520 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 2
hs_code: 29209085
risk_code: 34-37
hazard_code: C
safety_code: 26-36/37/39-45-7-24/25-23
hazard_class: 8
packing_group: III
Speicherklasse: 8A - Combustible corrosive hazardous materials
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B

Chemie und Industrie

Verwendung und Herstellung

U.S. Production2023: 1,000,000 - <5,000,000 lb

Consumer UsesIntermediate

Industry UsesHydraulic fluids

General Manufacturing Information · 2 Einträge

Utilities

Phosphorochloridic acid, diphenyl ester: ACTIVE

Anwendungen · 1 Eintrag

VerwendenDiphenyl chlorophosphate is used to prepare cyclohexyl-amidophosphoric acid diphenyl ester by reacting with cyclohexylamine. It is also used in the synthesis of alfa-substituted beta-lactams, anhydrides, esters and thioesters. It is also employed in the conversion of aldoximes to nitriles. Further, it is used in the preparation and reaction of enol phosphates, guanosine-adenosine-5',5'-triphosphate, guanosine-cytidine-5',5'-triphosphate, guanosine-uridine-5',5'-triphosphate, diguanosine-5',5'-diphosphate and diguanosine-5',5'-triphosphate. In addition to this, it serves as a phosphorylating agent for the preparation of 2-deoxy-D-galactose-3 and -6 phosphoric acids.

Darstellung · 1 Eintrag

synthetischeThe preparation of Diphenyl chlorophosphate is as follows:With a thermometer,Reflux condenser and mechanical agitation120 g of dichloromethane was placed in a 500 ml four-neck reaction flask.7.3 g of N,N-dimethylformamide,Stirring temperature control below 10 °C,Put 28g of bis(trichloromethyl) carbonate,A solution of 50 g of diphenyl phosphate and 120 g of dichloromethane was added.After the addition, the reaction was carried out for 3 hours. After the end of the reaction, the temperature was controlled below 10 ° C, 20 g of water was slowly added, and the mixture was stirred and the organic phase was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under normal pressure. The temperature was lowered to 0 ° C, and the insoluble matter was removed by filtration to obtain 48.9 g of diphenyl chlorophosphate. The purity of GC was 99.2%, and the yield was 90.3%.